Synlett 2025; 36(18): 3107-3111
DOI: 10.1055/a-2627-8548
Letter

Lewis Acid-Catalyzed Cyanomethylation of α,β-Unsaturated Keto Esters and Activated Ketones Using Vinyl Azide as an Acetonitrile Equivalent

Authors

  • Xudong Zhang

    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China (Ringgold ID: RIN66331)
  • Min Yang

    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China (Ringgold ID: RIN66331)
  • Jian Xiao

    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China (Ringgold ID: RIN66331)
  • Bin Chen

    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China (Ringgold ID: RIN66331)
  • Minghui Hui Xu

    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China (Ringgold ID: RIN66331)
  • Bin-Qin Wang

    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China (Ringgold ID: RIN66331)
  • Ping Hu

    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China (Ringgold ID: RIN66331)
  • Peng Cao

    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu, China (Ringgold ID: RIN66331)

Supported by: Sichuan Science and Technology Program 2022JDJQ0013,2022NSFSC1232
Supported by: National Natural Science Foundation of China 2022JDJQ0013,2022NSFSC1232


Graphical Abstract

Abstract

Lewis acid-catalyzed cyanomethylation reactions of α,β-unsaturated ketoesters and ketoamides with α-isopropanol vinyl azide were reported. The corresponding cyanoalkylated products were obtained in 40–97% and 45–96% yields, respectively, through 1,4- and 1,2-addition pathways.



Publication History

Received: 08 May 2025

Accepted after revision: 04 June 2025

Accepted Manuscript online:
04 June 2025

Article published online:
24 July 2025

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